ImageInWords (IIW) is a human-in-the-loop annotation framework that involves planning highly detailed image descriptions and generating a new dataset. This dataset achieves state-of-the-art results by evaluating automation and human parallel (SxS) metrics. The IIW dataset significantly improves in several dimensions while generating descriptions compared to previous datasets and the outputs of GPT-4V, including readability, comprehensiveness, specificity, imagination, and human similarity. Furthermore, models fine-tuned with the IIW dataset excel in text-to-image generation and visual language reasoning tasks, producing descriptions that are closer to the original images.